Vedaniti, Lear UNE Online Organic Compounds Containing Halogens Chapter - Chemistry JEE Main Concepts of Organic Compounds Containing Halogens for JEE Main Chemistry Organic halogen compounds are organic compounds that have had one or more hydrogen atoms replaced by an equal number of halogen atoms (F, Cl, Br, or I). Halogen atoms can be found in almost any type of organic substance (e.g., alcohols, ketones, and carboxylic acids) The boiling temperature, melting point, and density of an organic molecule increase when hydrogen is replaced with a halogen atom JEE Main Chemistry Chapters 2024Vedaniti, Lear NEOnlne ae A Tey 4 |Some Basic Concepts in 2 Blooe Elements Chemistry 2 | States of Matter D—and F — Block Elements 3 Atomic Structure Co-ordination Compounds Chemical Bonding and 4 iMeleciler Sinica Environmental Chemistry 5 Caan gnennadaaies Purification and Characterisation of Organic Compounds 6 | Solutions Goneral Organic Chemistry 7 | Equilibrium Hydrocarbons _ | Redox Reactions and Organic Compounds Containing Electrochemistry Halogens «| chemical kinetics Organic Compounds Containing Oxygen ra ‘Organic Compounds Containing Nitrogen “4 Classification Elements Dohme Periodicity Properties » General Principles and 12 | Processes of Isolation of Biomolecules Metals: 13 | Hydrogen Chemistry in Everyday Life 14 S* Block Elements 28 Principles Related to Practical Chemistry Important Topics of Organic Halogen Compounds ChapterVedaniti, Lear UNE Online + Alkyl halide * Allyl halide + Benzyl halide * Vinyl halide + Halo arenes + Swarts reaction + Finkelstein reaction + SN1 reaction * SN2 reaction Important Definition of Organic Compounds Containing HalogensVedaniti, Lear NEOnlne Allylic halides are the compounds in which the halogen Allyl halide atom is bonded to sp 3 -hybridised carbon atom next to carbon-carbon double bond (C=C). Vinyl halides are the compounds in which the halogen Vinyl halide atom is bonded to sp’ -hybridised carbon. A vinyl halide is a chemical compound with the formula CH.=CHX Benzyl chloride is a halogenated organic compound that Beneneme has the chemical formula CeH-CH:Cl A substitution reaction is a chemical reaction during Substitution reaction —_| which one functional group in a chemical compound is replaced by another functional group Sandmeyer reaction is a type of substitution reaction that is widely used in the production of aryl halides from aryl Giazonium salts. In this reaction, copper salts such as chloride, bromide, or iodide ions are utilised as catalysts Sandmeyer's Reaction A Grignard reagent or Grignard compound has the Grignard reagent general formula RMoX, where X is a halogen and R is an organic group, usually an alkyl or aryl Amethyl group is single-bonded to a carbonyl in the acetyl group. An acyl radical's carbonyl centro has one unbonded electron with which it makes a chemical bond with the molecule's remainder R. Acetyl group General Methods of Preparation:Vedaniti, Lear UNE Online + Organic compounds containing halogens, also known as alkyl halides or haloalkanes. are compounds in which one or more hydrogen atoms in hydrocarbons are replaced by halogen atoms (F, Cl, Br, I). These compounds can be prepared through various methods, including *Halogenation of Alkanes: Alkanes can undergo free radical halogenation in tho presence of halogens (Cly, Br2) and heat or ultraviolet (UV) light + Hydrohalogenation of Alkenes: Alkenes can react with hydrogen halides (HCI, HBr) to form alkyl halides in an addition reaction + Halogenation of Alcohols: Alcohols can be converted to alkyl halides by reacting them with phosphorus halides (PBr3, PCs). +Halogenation of Hydrocarbons: Aromatic compounds can be halogenated using nalogenating agents ike Bry /FeBrs (Bromination) or Cl / AICls (Chlorination) Properties and Reactions: * Alkyl halides have distinct properties and reactivity due to the polar nature of the carbon halogen (C-X) bond. Some key properties and reactions include +C-X Bond Polarity: The carbon-halogen bond is polar, with the halogen being more electronegative. This results in partial positive and negative charges on the carbon and halogen atoms, respectively. + Reactivity Towards Nucleophiles: The polar nature of the C-X bond makes alkyl halides susceptible to nucleophilic attacks. Nucleophiles, which are electron-rich species can attack the carbon atom, leading to substitution reactions. * Reactivity Towards Bases: Alkyl halides can also undergo elimination reactions when treated with strong bases. The base abstracts a proton from the adjacent carbon resulting in the formation of an alkene + Reactivity Towards Metals: Alkyl halides can react with motals like sodium (Na) or magnesium (Mg) to produce organometallic compounds, which are important intermediates in organic synthesis.Vedaniti, Lear UNE Online Nature of C-X bond The carbon halogen bond of an alkyl halide is polarised because halagen atoms are more electronegative than carbon atoms. The carbon atom has a partial positive charge, whereas the halogen atom has a partial negative charge. Fluorine atoms are the smallest, while iodine atoms are the largest, because the size of halogen atoms rises as we go down the group in the periodic table. As a result, the length of the carbon-halogen bond rises from C—F to C—I Reactions of Organic Compounds Containing Halogen 4. Nucleophilic Substitution Reaction A nucleophile combines with a haloalkane (the substrate) that has a partial positive charge on the carbon atom linked to halogen in this reaction. The halogen atom, also known as the leaving group, undergoes @ substitution process and becomes a halide ion. The substitution reaction is known as @ nucleophilic substitution reaction because it is triggered by a nucleophile. It is one of the most useful types of alkyl halide organic reactions in which the halogen is linked to sp® hybridised carbon. (a) Substitution nucleophilic bimolecular (SN?) reaction The reaction between CH,Cl and hydroxide ions to produce methanol and chloride ions follows second order kinetics, which means that the rate is determined by the concentrations of both reactants. The entering nucleophile reacts with the alkyl halide, breaking the carbon halide link while generating a new carbon-OH bond. There is no intermediary generated because these two processes occur simultaneously in a single phase. As a result, the attacked group's carbon atom structure invertsVedaniti, Lear NEOnlne Inversion of configuration is the term for this process. The carbon atom is simultaneously bound to the entering nucleophile and the outgoing leaving group in the transttion state, which makes such complexes unstable and unable to separate. Because the carbon atom in the transition state is connected to five atoms at the same time, itis unstable. Because this reaction necessitates the nucleophile approaching the carbon containing the leaving group, bulky substituents on or near the carbon atom have a significant inhibitory effect Because there are only three tiny hydrogen atoms in methyl halides, they react the fastest in SN? reactions of all the simple alkyl halides. Because bulky groups obstruct approaching nucleophiles, tertiary halides are the least reactive. As a result, the following is the order of reactivity: Primary halide > Secondary halide > Tertiary halide. P| QP Nu | Nu | NS Nu: —, ony oy my oy beng 4] Methyl Ethyl 1° Isopropyl 2° tert-butyl 3° (30) (1) (0.02) (0) (b) Substitution reaction SN‘ In most cases, SN’ reactions are carried out in polar protic solvents (like water, alcohol, acetic acid, etc.). The reaction of tert-butyl bromide with hydroxide ion produces tert-butyl alcohol and follows first-order kinetics, which means that the rate of reaction is determined by the concentration of only one reactant, tert-butyl bromide. It happens in two stages. The polarised C—Br bond is slowly cleaved in step |, yielding a carbocation and a bromide ion. In step Il, the carbocation is attacked by a nucleophile to complete the substitution reaction CH 3Vedaniti, Lear UNE Online 9 (CH,),CBr 24, + Br H,¢ CH, CH, + OH © step ad tn ae (CH,),COH 3 3 The first step is the slowest and most reversible. it entails the breakdown of the C-Br bond, for which the energy is produced by solvating halide ions with the proton of a protic solvent Because the reaction rate is determined by the slowest step, the rate is determined solely by the concentration of alkyl halide and not by the concentration of hydroxide ion. Furthermore, the higher the stability of a carbocation, the easier it will be to generate it from an alkyl halide and the faster the process will be. Because of the great stability of 3° carbocations in alkyl halides, 3° alkyl halides undergo SN' reaction fairly quickly. The sequence of reactivity of alkyl halides towards SN’ and SN? reactions can be summarised as follows For S,2 reaction —_—_—_— Tertiary halide; Secondary halide; Primary halide; CH,X OOOO For S,1 reaction 2. Halogen Exchange Reaction Alkyl iodides are frequently made by reacting alkyl chlorides/bromides with sodium iodide in dry acetone. The Finkelstein reaction is the name for this reaction R-X + Nal > R+l + NaXVedaniti, Lear UNE Online x= Cl, Br The best way to make alkyl fluondes is to heat an alkyl chloride ar bromide in the presence of a motallic fluoride such as AgF, Hg,F,, CoF,, or SbF,. The reaction is termed as the Swarts reaction CH,-Br + AGF — CH,-F + AgBr 3. Elimination Reaction When a haloalkane containing a -hydrogen atom is heated with an alcoholic potassium hydroxide solution, the hydrogen atom from the -carbon atom is removed, and a halogen atom from the -carbon atom is formed. As a result, an alkene is generated as a result of the reaction Beta hydrogen is eliminated in this reaction, which is known as a beta-elimination reaction in science, If more than one alkene could be created due to the availability of more than one -hydrogen atom, one alkene is usually synthesised as the primary product. o™ FA! —C*+¢— — > Sc=cO + B-H+ x7 / \ rp B= Base; X= Leaving group 4. Reaction with Metals The majority of organic chlorides, bromides, and iodides create carbon-metal bonds when they react with particular metals. Organometallic compounds are a type of compound that falls within this category (Grignard Reagent)Lear UNE Online CH,CH,Br + Mg SSthe, cH cH MgBr Grignard reagent 5. Wurtz Reaction In the dry ether, alkyl halides react with sodium to produce hydrocarbons with double the number of carbon atoms as the halide. The Wurtz reaction is the name for this reaction. 2RX +2Na — RR + 2NaX 6. Substitution Reaction in Haloarenes By heating chlorobenzene in an aqueous sodium hydroxide solution at 623K and 300 atmospheres, chlorobenzene can be transformed into phenol. The reactivity of haloarenes is increased by the presence of an electron-withdrawing group (-NO,) at ortho- and para- positions. OH QO _{i) NaOH, 623K, 300 atm_ NaOH, 623K, 300 atm OQ OH (i) NaOH, 443K _~ 1@Lear UNE Online a Won ma NO = z :Ck OH NO, NO, (i) NaOH, 368K (ii) He NO, NO, Ck H ON NO, O.N. -NO, warm qq > H,O NO, NO, 7. Electrophilic Substitution Reactions The electron density grows higher in ortho- and para-positions than in meta-positions due to resonance. -—x cl 1,2 - Dichlorobenzene (Minor) 1,4 - Dichlorobenzene (Major) B. Nitration cl cl cl NO, HNO, —_+ + conc. H,SO, 1- Chloro-2-nitrobenzene NO. (Minor) 7Lear UNE Online 1- Chloro-4-nitrobenzene (Major) C. Sulphonation cl cl cl SO,H + 2- Chlorobenzenesulfonic acid SO,H (Minor) 4- Chlorobenzenesulfonic acid (Major) D. Friedel Craft Alkylation cl cl cl Anhyd, AICI, CH, oo + CH,Cl * 1- Chloro-2-methylebenzene (Minor) CH, 1- Chloro-4-methylebenzene (Major)Lear UNE Online E. Fridel Craft Acylation cl cl o cl ? + H,c—E-cl Anhyd. AICI, cH, + 2- Chloroacetophenone CH, (Minor) 4-Chloroacetophenone (Major) 8. Wurtz-Fittig Reaction When an alkyl halide and an aryl halide are combined with sodium in dry ether, the result is an alkyl arene, which is known as the Wurtz-Fittig reaction. x R + Na+Rx ther, + Nax 9. Fittig reaction When aryl halides are treated with sodium in dry ether, two aryl groups are linked together to form similar compounds. It's known as the Fittig reaction ry + 2Na ther, C1 2NaxVedaniti, Lear UNE Online Na NIX Nm Diphenyl Uses, Environmental Effects of Chloroform, lodoform, Freons, and DDT In the study of organic compounds containing helogens, it's essential to understand the uses and environmental effects of certain halogenated compounds like chloroform, iodoform, freons, and DDT. Chloroform (CHCl): Uses: Chloroform has been historically used as an anesthetic in medical and dental procedures. It was once used in the production of refrigerants but has been largely replaced due to environmental concems. Environmental Effects: Chloroform is classified as a volatile organic compound (VOC), contributing to air pollution It can contamingte groundwater when disposed of improperly. posing a risk to aquatic ecosystems. CH lodoform ( ) Uses lodoform has antiseptic properties and was used in early medical practice. It's employed in organic synthesis and as a reagent for detecting the presence of methyl ketones Environmental Effects: lodoform itself is not known to be particularly harmful to the environment, but its production can involve hazardous chemicals.Vedaniti, Lear UNE Online Freons (Chlorofluorocarbons - CFCs): Uses CFCs, such as CFC-12, were widely used as refrigerants and propellants in aerosol sprays. They found applications in air conditioning and as solvents in various industries Environmental Effects: CFCs have been recognized for their detrimental impact on the ozone layer in the stratosphere, leading to the formation of the ozone hole. The ozone layer protects Earth from harmful ultraviolet (UV) radiation. The release of CFCs contributes to ozone layer depletion and increased UV exposure DDT (Dichlorodiphenyltrichloroethane): Uses DDT was one of the first synthetic insecticides and played a crucial role in controlling disease vectors like mosquitoes, reducing malaria and typhus transmission It was also used in agriculture to combat crop-damaging pests Environmental Effects: DDT is highly persistent in the environment and can accumulate in the food chain It has been linked to adverse effects on non-target organisms, including birds and aquatic life The bioaccumulation of DDT can lead to biomagnification, causing ecological imbalances. DDT is associated with long-term health concerns, including its potential carcinogenicity and endocrine-disrupting properties. JEE Main Organic Compounds Containing Halogens Solved Examples 1. Which of the following pairs of halogen compounds performs the SN‘ reaction first? (i)Vedaniti, Lear UNE Online anu (ii) Cl Ans: The rate of reaction for SN’ type of reaction depends upon the stability of carbocation. In this part, tertiary carbocation and secondary carbocation are present. The stability of tertiary carbocation is higher than that of the secondary carbocation. As a result, the SN‘ reaction of the tertiary carbocation will be accelerated In this part, secondary carbocation (2-chloroheptane) and primary carbocation (chlorohexane) are present. Secondary carbocation is more stable than primary carbocation. Therefore, secondary carbocation (2-chloroheptane) will undergo a faster SN reaction Key Points to remember: Order of rate of reaction for SN1 reaction is 1°> 2°> 3° 2. Write the equations for the preparation of 1-iodobutane from *1-butanol * 1-chlorobutane * but-1-eneLear UNE Online redP/I CH,CH,CH,CH,;OH ———*>CH,CH,CH,CH,I 1- butanol 1- iodobutane CH,CH,CH,CH,Cl + Nal —> CH,CH,CH,CH,| + NaCl 1- chlorobutane 1- iodobutane CH,CH,CH = CH, + Hl —> CH,CH,CH,CH,I But-1-ene 1- iodobutane Key points to remember: In saturated naloalkane, iodoalkane can be formed by the ion exchange method while in unsaturated alkane, iodoalkane can be formed by the addition reaction Solved Problems of Previous Year Question from the Chapter 4. The major product of the following reaction isVedaniti, Lear UNE Online Ans: The correct answer is option (c).Lear UNE Online Trick: This reaction will follow Hoffman's bromamide degradation reaction. The aliphatic diazonium salt is not stable, it gets converted into alcohol 2. In the following sequence of reactions, the P is: cy! +Mg dry [A] ethanol P ether (Major Product) wy Cs wy COT HCH, oO Om Ans: The correct answer for this question is the fourth option. cy ¥ Mg _ary ether, ether, cyaLear UNE Online Grignard Reagent C,H,-OH -+ cro — + + C,H,OMgcl cyclopentane Trick: This will follow the Grignard reagent reaction. Grignard reagent on reacting with an alcohol forms alkane. 3. Given below are two statements: one is labelled as Assertion (A) and the other is labelled as Reason (R). * Assertion (A): Synthesis of ethyl phenyl ether may be achieved by Williamson synthesis. * Reason (R): Reaction of bromobenzene with sodium ethoxide yields ethyl phenyl ether. In the light of the above statements, choose the most appropriate answer from the options given below: a. Both (A) and (R) are correct and (R) is the correct explanation of (A). b. (A) is correct but (R) is not correct. ¢. Both (A) and (R) are correct but (R) is NOT the correct explanation of (A). d. (A) is not correct but (R) is correct. Ans: The correct answer is b. ONa O—CH,CH, A acum. 1 Y 4+ NaRrVedaniti, Lear UNE Online KA ese NY ou Sodium Ethyl bromide Ethyl! phenyl Ether Phenoxide . Due to double bond character. <——. ~ + it does not involve in substitution reaction + C,H,ONa —> No Reation Trick: Resonance with the benzene ring creates a partial double bond in the compound Practice Questions 1. In the SN? reaction with -OH, which chemical in each of the following pairs will react faster? a. CH,Br or CH,I b. (CH,),CCI or CH.CI Ans: a. CHI b. CH,CI 2. Out of C,H,CH,CI and C.H,CHCIC.H,, which is more easily hydrolysed by aqueous KOH. Ans: C,H,CH,ClI JEE Main Chemistry Organic Compounds Containing Halogens Study Materials Here, you'll find a comprehensive collection of study resources for Organic Compounds Containing Halogens designed to help you excel in your JEE Main preparation. These materials cover various topics, providing you with a range of valuable content to support your studies. Simply click on the links below to access the study materials of Organic Compounds ContainingVedaniti, Lear NEOnlne Halogens and enhance your preparation for this challenging exam. JEE Main Orga Compounds Cont Oe eS ea JEE Main Organic Compounds Containing Halogens Notes JEE Main Organic Compounds Containing Halogens Important Questions JEE Main Organic Compounds Containing Halogens Practice Paper JEE Main Chemistry Study and Practice Materials Explore an array of resources in the JEE Main Chemistry Study and Practice Materials section. Our practice materials offer a wide variety of questions, comprehensive solutions, and a realistic test experience to elevate your preparation for the JEE Main exam. These tools are indispensable for self-assessment, boosting confidence, and refining problem-solving abilities, guaranteeing your readiness for the test. Explore the links below to enrich your Chemistry preparation By Cn ae Cee ae ta eC JEE Main Chemistry Previous Year Question Papers JEE Main Chemistry Mock Test JEE Main Chemistry Formula JEE Main Sample Paper JEE Main Chemistry Difference Between Conclusion The study of organic compounds containing halogens is of paramount importance in the world of chemistry. This JEE Main chapter provides a deep insight into the properties, nomenclature, synthesis, and reactivity of these compounds. Understanding their uses, as well as their environmental effects, is critical in promoting responsible chemical practices. This knowledge pauing FF Main chidants with the tanle ta eamnrahend the cinnificance af custainahleVedaniti, Lear UNE Online chemistry and the potential ecological impacts of halogenated compounds. 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